*** This bug is a duplicate of bug 1848309 ***
    https://bugs.launchpad.net/bugs/1848309

Confirming this is related to bug #1848309 except in this case was
caused by VBoxService.

$ systemctl status systemd-timesyncd                                            
           
● systemd-timesyncd.service - Network Time Synchronization                      
                         
   Loaded: loaded (/lib/systemd/system/systemd-timesyncd.service; enabled; 
vendor preset: enabled)       
  Drop-In: /lib/systemd/system/systemd-timesyncd.service.d                      
                         
           └─disable-with-time-daemon.conf                                      
                         
   Active: inactive (dead)                          
Condition: start condition failed at Mon 2020-01-06 22:27:32 AEDT; 4min 17s ago 
                         
           └─ ConditionFileIsExecutable=!/usr/sbin/VBoxService was not met
     Docs: man:systemd-timesyncd.service(8)                                     
                         
                                                                                
                         
Jan 04 17:09:56 ubuntu systemd[1]: Condition check resulted in Network Time 
Synchronization being skipped.


After purging virtualbox-guest-utils and virtualbox-6.0, ntp sync was 
successful:

$ systemctl status systemd-timesyncd.service                                    
            
● systemd-timesyncd.service - Network Time Synchronization
   Loaded: loaded (/lib/systemd/system/systemd-timesyncd.service; enabled; 
vendor preset: enabled)
  Drop-In: /lib/systemd/system/systemd-timesyncd.service.d
           └─disable-with-time-daemon.conf                                      
                                                                                
                                                  
   Active: active (running) since Tue 2020-01-07 10:59:06 AEDT; 4min 14s ago    
                                                                                
                                                  
     Docs: man:systemd-timesyncd.service(8)                                     
                                                                                
                                                  
 Main PID: 10499 (systemd-timesyn)                                              
                                                                                
                                                  
   Status: "Synchronized to time server for the first time 
[2001:67c:1560:8003::c7]:123 (ntp.ubuntu.com)."                                 
                                                                       
    Tasks: 2 (limit: 4915)                                                      
                         
   Memory: 1.7M                          
   CGroup: /system.slice/systemd-timesyncd.service                              
                         
           └─10499 /lib/systemd/systemd-timesyncd   
                                                                                
                         
Jan 07 10:59:06 ubuntu systemd[1]: Starting Network Time Synchronization...
Jan 07 10:59:06 ubuntu systemd[1]: Started Network Time Synchronization.        
                         
Jan 07 11:03:17 ubuntu systemd-timesyncd[10499]: Synchronized to time server 
for the first time [2001:67c:1560:8003::c7]:123 (ntp.ubuntu.com).

** This bug has been marked a duplicate of bug 1848309
   "Automatic Date & Time" doesn't reflect the service status

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https://bugs.launchpad.net/bugs/1858095

Title:
  'Automatic Date and Time' automatically disabled when trying to enable

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